|Preferred IUPAC name
3D model (JSmol)
|Molar mass||94.16 g·mol−1|
|Melting point||42 to 46 °C (108 to 115 °F; 315 to 319 K)|
|Boiling point||96 °C (205 °F; 369 K)|
|Flash point||−15 °C (5 °F; 258 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between C-3 and C-6. The molecule carries a double bond which induces significant ring strain and significant reactivity.
Norbornene is made by a Diels-Alder reaction of cyclopentadiene and ethylene. Many substituted norbornenes can be prepared similarly. Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane which is prepared by hydrogenation of norbornene.
Certain substituted norbornenes undergo unusual substitution reactions owing to the generation of the 2-norbornyl cation.
Norbornenes are important monomers in ring-opening metathesis polymerizations (ROMP). Typically these conversions are effected with ill-defined catalysts. Polynorbornenes exhibit high glass transition temperatures and high optical clarity.
In addition to ROMP, norbornene monomers also undergo vinyl-addition polymerization.
Polynorbornene is used mainly in the rubber industry for anti-vibration (rail, building, industry), anti-impact (personal protective equipment, shoe parts, bumpers) and grip improvement (toy tires, racing tires, transmission systems, transports systems for copiers, feeders, etc.)
- Norbornene MSDS
- Paul Binger, Petra Wedemann, and Udo H. Brinker. "Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene". Organic Syntheses. ; Collective Volume, 10, p. 231
- Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto. "2-Cyclohexene-1,4-dione". Organic Syntheses. ; Collective Volume, 9, p. 186
- Thansandote, Praew; Chong, Eugene; Feldmann, Kai-Oliver; Lautens, Mark (21 May 2010). "Palladium-Catalyzed Domino C−C/C−N Coupling Using a Norbornene Template: Synthesis of Substituted Benzomorpholines, Phenoxazines, and Dihydrodibenzoxazepines". The Journal of Organic Chemistry. 75 (10): 3495–3498. doi:10.1021/jo100408p. PMID 20423091.
- Lionel Delaude, Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01.